4-hydroxynaphthalene-1-arylketones and process of making such products



Patented Sept. 8 1925.

UNITED STATES rATEN OFFICE.

. summons DE MONTMOLLIN, mm. mm, emu'mn mum, m oann enema,

F BASEL, SWITZERLAND, ASSIGNORS BASLE, OF BASEIJ, SWITZERLAND.

4-HYDROXYNAPHTHALENE-l-ABYLKETONES a raonuc'rs.

Ho Drawing.

manner if derivatives of the 4-hydroxynaphe thalene-l-arylketones, which contain acid, groups in their 3-position, such as the 3-sulfonic acids and the 3-carboxylic acids of the 4-hydroxynaphthalene-1 arylketones, which are manufactured for examplein accordance with the processes described in the U. S. Patent No. 1,453,659 issued May 1st,-

1923, and the U. S. atent application Serial No. 575579, filed uly 17th, 1922, are heated preferably in the presence of a suitable liquid or diluent respect ively. The

compounds thus obtained correspond with the general formula: v

in which R is an unsulfonated and uncarboxylated aryl radical which neither coni tains sulfo nor carboxyl groups, but which may contain other substituents. They'represent whitish powders which dissolve in caustic soda solution to a yellow solution.

The following examples illustrate-the in- 0 vention without, however, restricting the same.

Ewaxmple '1, 5

100 parts of the l-phenylketonel-hydroxynaphthalene-S-sulfonic acid are heated 4 in a closed vessel with 400- parts of sulfuric acid of 5% strength at ISO-190 C. There is obtained the c-hydroxynaphthalene lphenylketone nearly pure which may be crystallized from benzene.

Example 2.

100 parts of the 1- (2-chloro)phenylketone 4 hydroxynaphthalene 3 carboxyli c Application and January so, was. Berlal in". e1d.aio

.ro socm'nr or summon. nmus'rmr m or we even acid are heated cautious y th100 parts of dimethylaniline at.110150 C. until evolut1on of carbon dioxide has ceased. -From the cooled. mass there crystallizes the 1- (2- chloro) phenylketone-4-hydroxynaphthalene. Recrystallized from acetic acid it-melts at 216 0., the correspondin --1- (4' -"chlor o)- phenylketonel-hydroxynap thalene at 210 0., and the 1-(2', 4-dichloro) phenylketone- 4-hydroxynaphthalene at 222? C.-

V I Example v 100 parts of the 1-ch1oro-2," 1-dinaphthylketonei-hydroxy-3-carboxylic acid are I heated in a closed vessel with 300 parts of sulfuric acid of 5%v strength at 180190 C.

There is obtained the l-chloro-y-hydroxy '2, 1'-dinaphthylketone nearly pure which when crystallized from dilute acetic acid melts at 213 C. I y

I mam '100 parts of the 4 y-dihydroxy-l, 1"-dinaphthylketone-3, 3 -dicarboxylic acid are heated slowly with400 parts of dimethylanil1ne at 150 C. until evolution of carbon dioxide has ceased. The 4, 4'-dihydroxy 1, 1'-dinaphthylketone liberated from the dimethylaniline may be crystallized from wa'ter as a sodium salt or, for example, from acetic acid as a free acid. What we claim is: 1. The herein described process manufacture of 4-hydroxynaphthalene-1- arylketones consisting in heating derivatives of the 4-hydroxynaphthalene-1-a lketones which contain acid groups in thdif 3-posi tion. r

2. The herein describedprocess for the manufacture of 4-hydroxynaphthalene-L arylketones consisting in heating derivatives of the 4-hydroxynaphthalene-l-arylketones which contain acid groups in their 3-position in the presence of a diluent. j

3. The herein described new 4-hydroxynaphthalene-l-arylketones of. the general formula y v for the I in which R is an unsulfonated and uncar in which R is an unsulfonated and uncarboxylated aryl radical containing at least boxylated benzene nucleus containing at 15 one halogen atom, which represent whitish least one halogen atom, which represent powders dissolving in caustic soda solution whitish powders dissolving in caustlo soda 6 to a yellow solution. solution to a. yellow solution.

4. [he herein described new 4-hydr0xy- In witness whereof we have hereunto naphthalene-l-arylketones of the general signed our names this 17th day of January 20 formula 1923.

o H0 00; I DE EMIL REBER.

, GERALD BONHOTE.

'JOSEF SPIELER. 

